Strategy Session Facilitation with Design Thinking & Liberating Structures

Strategy Session Facilitation with Design Thinking + Liberating Structures

Because brainstorming & group thinking is notoriously ineffective

We need a better way for collective decision making, especially for when stakes are high

Takeshi Yoshida, Lifecycle

Takeshi Yoshida

Chief Coach & Founder

Agile Organization Development


Why brainstorming doesn’t work

That was fun, but… Why do we get that slight, lingering feeling of doubt and dissatisfaction after brainstorming sessions?

Here’s why:

  • Group dynamics: 80/20 rule applies.
    • Domination: The vocal minority dominate the space, crowding out the voices of the rest.
    • Judgment and hesitation: Our fear of being wrong and looking stupid makes us shut up.
    • Ideas evaporate: We can’t really listen and think at the same time, so our nascent ideas quickly dissipate while waiting for our turn to speak.
    • Social loafing: We become mentally lazy in groups – let others do the thinking!
  • Linear outcome: It’s so hard to do dissociated thinking (thinking of something separate – out of the box) during a group conversation.
    • Anchoring bias, recency bias: The vocal minority, often the leader of the group, speaks up first, and unintentionally sets the tone of the discussion which will carry to the end. And as we place priority to the last piece of information heard, we tend not to deviate from the chain of discussion, making the conclusion somewhat predictable.
    • False-consensus effect, bandwagon effect: We tend to think that others think like we do. So if the vocal minority hears no disagreement, they take that as an agreement. And if everyone seems to be agreeing, we tend to follow too.

Brainstorming doesn’t unleash the potential of the group, rather it makes each individual less creative.

Bringing together the best of divergent and convergent thinking

However, the one good thing about brainstorming is that, it brings people together. Working towards a group consensus in a high energy, participatory way produces a strong sense of collective achievement.

So, while brainstorming misses out on the strength of divergent thinking with individuals, it does tap into the strength of convergent thinking with the group.

Now that we know this, we just need to think of better ways to facilitate group thinking that excels in capturing both strengths of divergent and convergent thinking of the individual and group.

Design Thinking

Design Thinking is a powerful cognitive and action framework that not only helps idea generation better, but goes all the way to testing those ideas and iterating the process until ideas that work are nailed.

It is naturally a group process that is aimed to activate the creativity in everyone. A notable characteristic in the Design Thinking process is in the divergent and convergent “double diamond”:

Design Thinking fish diagram by Lifecycle |

  1. Empathize: For any given challenge, the team first identifies who are the customers, stakeholders, partners and other “actors” in the scene, and start with a divergent exercise of understanding them, e.g. their wants and needs.
  2. Define: And then the team moves onto converging those thoughts into a problem statement, e.g. “Customer needs a way to…, because… It would be great if we can…”
  3. Ideate: Next, the team diverges into generating many solution ideas for solving the problem; i.e. “How might we…?”
  4. Prototype: The team then converges those ideas into a choice of a single or small set of solutions that they will build a prototype – something that will allow them to test the validity of problem statement (“Are we solving the right problem?”) and the solution (“Is this solution solving the customer’s problem?”).
  5. Test: Finally, the team sets up an opportunity to test the prototype to validate its effectiveness. The most important part is the learning – clearly it’s not expected to nail the solution in one go, and the objective here is measurement and feedback into any of the Design Thinking process to iterate and experiment for a more effective solution.

Another important attribute is that, as with many other Agile approaches, Design Thinking is process driven, but not fixed process. In fact, because of the highly creative nature of the approach, Design Thinking can be a non-linear process:

Design Thinking is Non-Linear |

Strategy session facilitation with Design Thinking

The beauty of Design Thinking is that it can be done in any scale. We can do it as a quick 30 minute table exercise, a one or two day workshop, or make it into a full few days lab and field experiment.

I very like using Design Thinking as the basic framework for strategy formation. Often when we are in problem solving mode, we don’t separate the problem and solution. Thinking of what and how separately allows us to clarify and explore better – ultimately leading to better outcomes. Another trap that we often fall into is, not recognizing that ideas are hypotheses, and solutions are not real solutions yet until proven effective. Design Thinking forces us to test, measure and validate our assumptions and actions. And by doing this in iteration with light-weight prototypes, it is a very fast and cost effective way to find solutions in complex challenges.

Liberating Structures

Often in combination with Design Thinking, my other go-to facilitation toolkit is Liberating Structures.

Liberating Structures is a collection of powerful team exercises curated by Henri Lipmanowicz and Keith McCandless ( Currently there are 33 exercises listed on Henry and Keith’s website. I also share my session instructions slides with abbreviated instructions and modified content here:

Here are some of my favorites:


The first step of 1-2-4-All is a solo exercise where people write down their thoughts individually. This is a subtle yet incredibly important point: it directly addresses the many problems of group thinking in brainstorming mentioned above.

Individuals ideas are next shared in groups of 2, 4 and finally with the whole group. During this process there will be divergence and convergence of ideas, through repeat sharing and consensus building.

Jake Knapp, author of the Design Sprint book, coined the term “Thinking alone, together” for alternative ways of group thinking. 1-2-4-All is one such way. It’s quick, easy and effective. I regularly use this for my sessions.

Min Specs

Min Specs is an example of a Liberating Structure that I often use with Design Thinking.

In Agile, whether it is Design Thinking, Lean Startup or Scrum, we build prototypes and MVPs (minimum viable products) to test the market first. We do this in iteration before building a full product so that we can prevent ourselves from building something that people won’t buy.

The challenge is that a lot of us have a tendency to start building a full product from the get-go. Even if it’s not a full product, still, we try to make a pretty meaty one.

A completely stripped down, lean version of the product, is something that is hard to imagine for many of us. This is a simple yet powerful exercise that addresses the challenge.

DAD – Discovery & Action Dialogue

We have a chronic challenge – a recurring problem X.

Let’s find Positive Deviant Behaviors and practices that will help us solve this problem.

Ecocycle Planning

Organizations are systems. Organizations will always be in a state of equilibrium, but that doesn’t necessarily mean it’s in an optimum state with respect to the organization’s objectives set by its members.

In Ecocycle Planning, we address organizational inefficiencies and resource allocation imbalance by tackling two traps: poverty trap, and rigidity trap.

Ecocycle Planning - Liberating Structures

25/10 Crowd Sourcing

Crazy 8, Jake Knapp

I like to do this exercise after individually brain-spilling for ideas with a separate exercise called Crazy 8.

After individually selecting the one best idea from the eight, we go into 25/10 and let the ideas compete in the group.

It’s good to keep the ideas anonymous during the 25/10. That would let the ideas go through the iterative scoring without anchoring or bias, and will let the genuinely best idea emerge as the group’s choice.

15% Solutions

This is a great exercise to identify low hanging fruit, immediately actionable solutions.

WINFY: What I Need From You

But of course, all organizations can’t get away from dependency challenges.

Use this exercise to sort them out.

What, So What, Now What?

This is my favorite closing exercise. I use it almost every session.

The exercise allows participants to recap the learnings, think of the relevancy of those learnings for themselves, and make each individual accountable for next step actions.

Visit here for more Liberating Structure ideas:

All pieced together…

This is what we can get done in three hours! An example of a facilitated strategy session with Design Thinking + Liberating Structures:

PDF version: Design Thinking + Liberating Structures facilitated workshop design example – 3 hour session

  • Join the Mental Model Dōjō Learning Community

    Upcoming Dōjō Session

    The Art of Upward Management with Authenticity – Building Productive Relationships with Demanding Leaders

    Community Sign-Up

    Join our Mental Model Dōjō learning community and receive Knowledge Base and YouTube channel updates and invitations to community events.

    Joining the the Mental Model Dōjō learning community is free. Agile Organization Development, managed by Lifecycle Pte. Ltd., is committed to protecting and respecting your privacy, and we’ll only use your personal information to administer your account and to provide the products and services you requested from us. From time to time, we would like to contact you about our products and services, as well as other content that may be of interest to you. You may unsubscribe from these communications at any time. For more information on how to unsubscribe, our privacy practices, and how we are committed to protecting and respecting your privacy, please review our Privacy Policy. By clicking submit, you consent to allow Lifecycle Pte. Ltd. to store and process the personal information submitted.

Follow Coach Takeshi:

Takeshi Yoshida, Founder & Chief Coach, Agile Organization Development

About Agile OD: We are a tribe of learning professionals that help organzations succeed in change, transformation, innovation | Coach Takeshi bio & credentials